The story Puddi'n' Head Wilson has many characters, however there are only two that can be considered to be main characters. These are Roxy and Tom Driscoll.

At the beginning of the story, Roxy is a slave of about 20 - 25 years old. Roxy is only 1/16 black - and has white skin, however this still qualifies her as a slave. She has just given birth to her first child, which she named Chambers. Since Chambers has a white father he is only 1/32 black, but like his mother, he is still a slave. Roxy loves her son very much. This is evident by the statement, "killin' him would save him fum goin' down de river." She loves him so much that she switches her son with her master's so that Chambers will not have to endure the life of a slave.

When her master dies, Roxy is set free. She takes advantage of her new opportunities and spends the next eight years as a chambermaid on a steamboat traveling up and down the Mississippi River. She is very wise in investing her earnings in a bank in New Orleans. However, when she finally decides to retire, she finds out that "the bank had gone to smash and carried her four hundred dollars with it."

This loss of money sends Roxy back to Dawson's Landing in order to try to live off of her real son known as Tom Driscoll. Back at Dawson's Landing, Roxy loses her innocence. She and her son stoop to stealing in order to pay for his gambling deficits and to make money for her to live on. During the story, Roxy's character makes a lot of changes. Most of them are for the worse.

The other main character is Roxy's son. His real name was Valet de Chambre, however from now on, will be adressed as Tom Driscoll. "Tom was a bad baby, from the very beginning..." This trait carried over into his older life as well. He was very stuck up and mean to any one that he disagreed with. One of his favorite activities growing up was "cuffing and banging and scratching Chambers, unrebuked." Later on Tom went to Yale, however he stayed there only two years and studied nothing in particular (he did, however, learn the art of gambling). So he was without a way to get a consistant income. This among other things greatly frustrated his uncle, who had adopted him after the death of his father.

Tom is desperate to keep his uncle happy and to keep the will - making him the heir to his uncle's estate - intact. This causes him to rob the other citizens of the town in order to pay off his debts from gambling. Eventually he becomes so desperate that he tries to rob from his uncle who catches him. Tom is so suprised that he murders his own uncle. Tom never really learns from his mistakes, and is always a cruel, unloving person.